CN107226806A - 用于有机电致发光元件的化合物及使用该化合物的有机电致发光元件 - Google Patents
用于有机电致发光元件的化合物及使用该化合物的有机电致发光元件 Download PDFInfo
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- CN107226806A CN107226806A CN201610281621.0A CN201610281621A CN107226806A CN 107226806 A CN107226806 A CN 107226806A CN 201610281621 A CN201610281621 A CN 201610281621A CN 107226806 A CN107226806 A CN 107226806A
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 11
- 230000004888 barrier function Effects 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
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- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical class BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 2
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 2
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- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
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- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- PBSIVXAPTBHFFV-UHFFFAOYSA-N [4-(1-phenylbenzimidazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 PBSIVXAPTBHFFV-UHFFFAOYSA-N 0.000 description 1
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
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- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 238000010295 mobile communication Methods 0.000 description 1
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 238000004062 sedimentation Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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Abstract
本发明提供了一种新颖的式(I)化合物及使用该化合物的有机电致发光元件,其中,X1、A1及n如说明书中的定义。藉由本发明提供的式(I)化合物,可改善有机电致发光元件的稳定性,并降低操作电压。
Description
技术领域
本发明有关一种用于有机电致发光元件的化合物及使用该化合物的有机电致发光元件。
背景技术
为满足有机电致发光元件(OLED)的应用,已更重视新颖有机材料的开发。这些元件因为在制造高发光率的高密度像素显示器上提供有成本优势,更具有长寿命、高效率、低驱动电压及广色域,而具商业性吸引力。
典型的OLED包括至少一夹置于阳极与阴极之间的有机发射(organic emissive)层。当施加电流时,阳极注入空穴且阴极注入电子至该一层或多层有机发射层,被注入的空穴及电子各自迁移(migrate)至相反的带电荷电极。当电子及空穴局限在相同的分子上时,形成“激子(exciton)”,该激子具有激发能态的局限化电子-空穴对。激子通过发光机制松弛而发射光。为了提升此等元件的电荷传输能力及发光效率,已于发光层旁结合一层或多层的额外层体,例如电子传输层及/或空穴传输层,或电子阻挡层及/或空穴阻挡层。US5707745及US 9153787已揭示在主体材料掺杂另一材料(客体),以提升元件性能及调整色度。
制造具多层薄膜结构OLED的原因包含使这些电极及有机层之间的界面安定。此外,在有机材料中,电子及空穴的迁移率(mobility)明显不同。因此,若使用相称的空穴传输及电子传输层,空穴及电子可有效地传输至发光层。此外,若发射层中空穴及电子的密度平衡时,可增加发光效率。适当的结合上述有机层可增进元件效率及寿命。然而,仍难以找到满足所有实际显示器应用需求的有机材料。
因此,亟需开发一种电子传输材料,以延长元件寿命,并可提高发光效率和维持低的驱动电压。
发明内容
本发明一目的在于提供一种具有高发光效率、低驱动电压及较长寿命的 用于OLED的材料。
本发明提供一种用于OLED的式(I)化合物:
其中,
X1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
A1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
X1、及A1为相同或相异;以及
n表示1或2的整数,当n表示2时,A1各自为相同或相异;且当X1为经取代或未经取代的(C6-C30)芳基时,n为1。
本发明还提供一种有机电致发光元件,包含:阴极;阳极;以及有机层,介于阴极与阳极之间,且该有机层包含上述式(I)化合物。
本发明的有机电致发光元件的有机层可为电子传输层、电子注入层、发光层、空穴阻挡层或电子阻挡层,且除了该有机层外,该有机电致发光元件还可包括不同于该有机层的电子传输层、电子注入层、发光层、空穴阻挡层及电子阻挡层所组成组的至少一层。
根据本发明,藉由本发明提供的式(I)化合物,可改善元件的稳定性,并降低操作电压。
附图说明
图1为本发明有机电致发光元件的一实施例的剖面示意图;
图2为本发明有机电致发光元件的另一实施例的剖面示意图;
图3为本发明有机电致发光元件的又一实施例的剖面示意图;以及
图4为本发明有机电致发光元件的电致发光光谱。
符号说明
100、200、300 有机电致发光元件
110、210、310 基底
120、220、320 阳极
130、230、330 空穴注入层
140、240、340 空穴传输层
150、250、350 发光层
160、260、360 电子传输层
170、270、370 电子注入层
180、280、380 阴极
245、355 激子阻挡层。
具体实施方式
以下藉由较佳实施例详细说明本发明,以使本领域技术人员易于了解本发明的说明书所揭示的益处及功效。
本文所述的范围与所揭露的值都包含边值且可合并。举例而言,当任何数值,例如一整数或点落入本文所述的范围时,则可以该点或数值做为下限或上限值而推导出次范围。此外,本文所例举基团,例如属于X1和A1的基团或取代基,皆可与其他基团合并于式(I)。
依据本发明,可应用于OLED的化合物如式(I)所示:
其中,X1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
A1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
X1及A1为相同或相异;以及
n表示1或2的整数,当n表示2时,A1各自为相同或相异;且当X1为经取代或未经取代的(C6-C30)芳基时,n为1。
于一具体实施例中,X1表示经取代或未经取代的(C6-C20)芳基、经取代或未经取代的(5至20元)杂芳基,该(5至20元)杂芳基含有至少一个选自由N、O及S所组成组中的杂原子。
于一具体实施例中,A1表示经取代或未经取代的(C6-C20)芳基、经取代或未经取代的(5至20元)杂芳基,该(5至20元)杂芳基含有至少一个选自由N、O及S所组成组中的杂原子。
于一具体实施例中,上述式(I)中的A1表示式(II)或式(III)化合物:
式(II)中,Ar1及Ar2各自独立表示未经取代的(C6-C20)(亚)芳基,式(II)化合物藉由Ar1或Ar2与式(I)化合物连接,或式(II)化合物藉由Ar1及Ar2与式(I)化合物形成稠合环;式(III)中,Z1表示N、O、S、CMe2或CH2,其中,当Z1为N时,式(III)化合物藉由Z1与式(I)化合物连接,且当Z1为O、S、CMe2或CH2时,式(III)化合物藉由其所具的苯基与式(I)化合物连接。
于一具体实施例中,当n为1时,该式(I)化合物为式(I-1)或式(I-2)所示:
于一具体实施例中,当n为2时,该式(I)化合物为式(I-3)所示:
文中,表达成“经取代或未经取代的”中的“经取代的”表示在某个官能团中的氢原子经另一个原子或基团(即取代基)置换。这些取代基各自独立为选自下列所组成组中的至少一者:氘;卤素;(C1-C30)烷基;(C1-C30)烷氧基;(C6-C30)芳基;(5至30元)杂芳基,其中该(5至30元)杂芳基可经(C6-C30)芳基取代;经(C6-C30)芳基取代的(5至30元)杂芳基;(C3-C30)环烷基;(5至7元)杂环烷基;三(C1-C30)烷基硅烷基;三(C1-C30)芳基硅烷基;二(C1-C30)烷基(C6-C30)芳基硅烷基;(C1-C30)烷基二(C6-C30)芳基硅烷基;(C2-C30)烯基;(C2-C30)炔基;氰基;二(C1-C30)烷基胺基;二(C6-C30)芳基胺基;(C1-C30)烷基(C6-C30)芳基胺基;二(C6-C30)芳基硼基;二(C1-C30)烷基硼基;(C1-C30)烷基(C6-C30)芳基硼基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基;羧基;硝基;及羟基。
于一具体实施例中,该(C6-C30)芳基经选自(C1-C10)烷基、(C6-C30)芳 基及(5至30元)杂芳基所组成组中的至少一种取代基取代,其中,该(5至30元)杂芳基经(C6-C30)芳基取代。
于一具体实施例中,该(5至30元)杂芳基经选自(C1-C10)烷基、(C6-C30)芳基及(5至30元)杂芳基所组成组中的至少一种取代基取代,其中,该(5至30元)杂芳基经(C6-C30)芳基取代。
于另一具体实施例中,该(C6-C30)芳基经选自(C1-C5)烷基、(C6-C10)芳基及苯并咪唑基所组成组中的至少一种取代基取代,其中,该苯并咪唑基经(C6-C10)芳基取代。
于另一具体实施例中,该(5至30元)杂芳基经选自(C1-C5)烷基、(C6-C10)芳基及苯并咪唑基所组成组中的至少一种取代基取代,其中,该苯并咪唑基经(C6-C10)芳基取代。
文中,“(亚)芳基”表示芳基或亚芳基。芳基指衍生自芳香烃的单环或稠环,且包括苯基、联苯基、联三苯基(terphenyl)、萘基、联萘基、苯基萘基、萘基苯基、芴基(fluorenyl)、苯基芴基、苯并芴基、二苯并芴基、菲基、苯基菲基、蒽基、茚基、联伸三苯基(triphenylenyl)、芘基、稠四苯基、苝基、蒯基(chrysenyl)、萘并萘基、丙二烯合芴基(fluoranthenyl)等。
文中,“(亚)杂芳基”表示杂芳基或亚杂芳基。(5至30元)杂芳基指含有选自B、N、O、S、P(=O)、Si、及P所组成组中的至少一个杂原子且具有3至30个环主链原子的芳基;为单环,或为与至少一个苯环缩合的稠环;为部分饱和;为通过一或多个单键链接至少一个杂芳基或芳基至杂芳基所形成者;及包括单环型杂芳基如,呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋呫基、吡啶基、吡嗪基、嘧啶基、哒嗪基等,及稠环型杂芳基如,苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹噁啉基、咔唑基、啡噁嗪基、啡啶基、苯并二噁茂基(benzodioxolyl)、二氢吖啶基等。
于一具体实施例中,X1选自下列所组成组中的一者:
及
于一具体实施例中,A1选自下列所组成组中的一者:
及
本发明还提供一种有机电致发光元件,包含:阴极;阳极;以及有机层,介于该阴极与阳极之间,且该有机层包含上述式(I)化合物。
前述式(I)化合物的优选实例选自但不限于下列1-1至1-10、2-1至2-10、3-1至3-10、4-1至4-10、5-1或2-10、6-1至6-10、7-1至7-10、8-1至8-10、9-1至9-10、10-1至10-10、11-1至11-10、12-1至12-10、13-1至13-10、14-1至14-10、15-1至15-10、16-1至16-10、17-1至17-10、18-1至18-10、19-1至19-10、20-1至20-10、21-1至21-10、22-1至22-10、23-1至23-10、24-1至24-10、25-1至25-10、26-1至26-10、27-1至27-10、28-1至28-10、29-1至29-10、30-1至30-10、31-1至31-10、32-1至32-10、33-1至33-10、34-1至34-11、35-1至35-11、36-1至36-11。
可采用如下所示反应路线1至6中所示的一系列反应以合成式(I)所示化合物,但不限于此。
将4-溴苯甲醛(4-bromobenzaldehyde)(50g,270.2mmol)、4-乙酰基联苯(4-Acetylbiphenyl)(55.68g,283.8mmol)及1000ml EtOH加入反应瓶中搅拌,再加NaO-t-Bu(Sodium tert-Butoxide,简称STB)(29.83g,310.8mmol)至反 应瓶中一起搅拌后,室温25℃反应隔夜(通氮气),过滤后以100ml水及100ml甲醇冲洗,固体再以400ml纯水与100ml甲醇搅拌15分钟后过滤重复2~3次,固体再以400ml甲醇搅拌15分钟过滤,固体再以400ml乙醇搅拌15分钟纯化过滤,65℃烘干得84.7g的白色固体中间体A,产率86.28%。
中间体A(20g,55.1mmol)与不同的氯化吡啶(pyridinium chloride)衍生物(60.6mmol)及200ml甲苯入反应瓶中搅拌,再加入STB(7.93g,82.6mmol)至反应瓶中一起搅拌后,温度100±5℃反应16小时(通氮气)。降温,加300ml乙酸乙酯(Ethyl Acetate,简称EA)后,以200ml纯水萃取4次,以无水硫酸钠除水过滤,浓缩后加甲醇析出过滤,以甲醇冲洗烘干得固体的中间体B。
将3-溴苯甲醛(3-bromobenzaldehyde)(50g,2702mmol)、4-乙酰基联苯(4-Acetylbiphenyl)(55.68g,2838mmol)及1000ml EtOH加入反应瓶中搅拌,再加STB(29.83g,3108mmol)至反应瓶中一起搅拌后,室温25℃反应隔夜(通氮气),过滤后以100ml水跟100ml甲醇冲洗,固体再以400ml纯水与100m甲醇搅拌15分钟后过滤重复2~3次,固体再以400ml甲醇搅拌15分钟过滤,固体再以400ml乙醇搅拌15分钟纯化过滤,65℃烘干得89.6g的白色固体中间体C,产率91.27%。
中间体C(20g,551mmol)与不同的氯化吡啶衍生物(606mmol)与200ml甲苯入反应瓶中搅拌,再加入STB(7.93g,826mmol)至反应瓶中一起搅拌后,温度100±5℃反应16小时(通氮气)。降温加300mlEA后以200ml纯水萃取4次,以无水硫酸钠除水过滤,浓缩后加甲醇析出过滤,以甲醇冲洗烘干得固体的中间体D。
将3,5-二溴苯甲醛(3,5-Dibromobenzaldehyde)(30g,1137mmol)、4-乙酰基联苯(4-Acetylbiphenyl)(23.42g,1194mmol)及600ml EtOH加入反应瓶中搅拌,再加STB(16.37g,1705mmol)至反应瓶中一起搅拌后,室温25℃反应隔夜(通氮气),过滤后以100ml水跟100ml甲醇冲洗,固体再以250ml纯水与50m甲醇搅拌15分钟后过滤重复2~3次,固体再以200ml甲醇搅拌15分钟过滤,固体再以250ml乙醇搅拌15分钟纯化过滤,65℃烘干得48.5g的淡黄色固体中间体E,产率98.49%。
中间体E(20g,551mmol)与不同的氯化吡啶衍生物(606mmol)与200ml甲苯入反应瓶中搅拌,再加入STB(7.93g,826mmol)至反应瓶中一起搅拌后, 温度100±5℃反应16小时,通氮气。降温加300mlEA后以200ml纯水萃取4次,以无水硫酸钠除水过滤,浓缩后加甲醇析出过滤,以甲醇冲洗烘干得固体的中间体F。
反应路线1
反应路线2
反应路线3
反应路线4
反应路线5
反应路线6
本发明还提供一种有机电致发光元件,包含:阴极;阳极;以及包含本发明式(I)化合物的有机层,介于该阴极与阳极之间。
式(I)所示化合物可应用于OLED的有机层。因此,本发明的OLED具有至少一层设置于基底上阳极与阴极之间的有机层,其中有机层包含如上列式(I)所示化合物。该有机层为发光层、空穴阻挡层、电子传输层、电子注入层或空穴传输层,且除了该有机层外,该有机电致发光元件还可包括不同于该有机层的电子传输层、电子注入层、发光层、空穴阻挡层及电子阻挡层所组 成群组的至少一层。包含式(I)所示化合物的该有机层优选为电子传输/注入层,可以式(I)所示化合物作为单一材料,或与n/p型导电掺杂剂(n/p type dopants)结合。于一具体实施例中,该电子传输层包含式(I)化合物。
应用于电子传输层的导电掺杂剂优选为有机碱金属/碱土金属络合物(organicalkali/alkaline metal complexes)、氧化物(oxides)、卤化物(halides)、碳酸盐(carbonates)及含有至少一种选自锂和铯金属的磷酸碱金属/碱土金属盐(phosphates ofalkali/alkaline group metals containing at least one metal selected fromlithium and cesium)。该有机金属络合物在上述专利或他处为已知,并可选择合适的有机金属络合物于本发明中使用。
以该有机层的重量计算,该导电掺杂剂的含量为0wt%至90wt%。例如,该有机层为电子传输层或电子注入层,前述导电掺杂剂于电子传输层/电子注入层中的含量优选25wt%至75wt%重量比的范围。
于一具体实施例中,该有机层是电子传输层。
于一具体实施例中,该电子传输层包含式(I)化合物与n型导电掺杂剂,且该n型导电掺杂剂的含量为大于0wt%至75wt%。
于一具体实施例中,以该有机层的重量计算,式(I)化合物的含量为25wt%至100wt%。又,该有机层的厚度为1纳米至500纳米。
于又一具体实施例中,该有机电致发光元件还包括电子传输层、电子注入层、发光层、空穴阻挡层及电子阻挡层所组成组的至少一层。而该发光层还包含荧光或磷光发射体。
于一具体实施例中,自该阳极至该有机层之间还包括空穴注入层、空穴传输层、发光层,且自该有机层至该阴极之间还包括电子注入层,且该有机层为电子传输层。
再者,式(I)所示化合物还可被用于发光层与电子传输层间的层。该发光层可包含荧光及磷光掺杂剂以及分别对应荧光或磷光掺杂剂的荧光及磷光发射主体。
进一步而言,由下式(I)所示化合物可被使用于电子注入/传输层或空穴阻挡层及/或电子阻挡层。
本发明的有机电致发光元件的结构将配合图式加以说明。
图1为本发明有机电致发光元件的一具体实施例的剖面示意图。有机电 致发光元件100包含基底110、阳极120、空穴注入层130、空穴传输层140、发光层150、电子传输层160、电子注入层170及阴极180。有机电致发光元件100可经由依序沉积上述各层来制作。图2为本发明有机电致发光元件另一具体实施例的剖面示意图。图2所示的有机电致发光元件与图1近似,除了包含基底210、阳极220、空穴注入层230、空穴传输层240、发光层250、电子传输层260、电子注入层270及阴极280,其不同之处在于激子阻挡层245设于空穴传输层240与发光层250之间。图3绘示本发明有机电致发光元件又一具体实施例的剖面示意图。图3所示的有机电致发光元件亦与图1近似,除了包含基底310、阳极320、空穴注入层330、空穴传输层340、发光层350、电子传输层360、电子注入层370及阴极380,其不同之处在于激子阻挡层355设于发光层350与电子传输层360之间。
亦可依图1至3所示元件的反置式结构(reverse structure)制造有机电致发光元件。于反置式结构中,可视需求增减一层或数层。
应用于空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、发光层及电子注入层的材料可选择常用材料。例如,形成电子传输层的电子传输材料不同于形成发光层的材料,且其具有传输空穴的性质,从而促成空穴于电子传输层中迁移,且防止因发光层与电子传输层的解离能差所导致的载子累积。
此外,US 5844363揭示一种结合阳极的可挠性透明基底,其全部内容为本发明所引用。如US 20030230980所例示p型掺杂的空穴传输层以摩尔比50:1于m-MTDATA掺杂F4-TCNQ,其全部内容为本发明所引用。如US 20030230980所例示n型掺杂的电子传输层以摩尔比1:1于BPhen掺杂锂,其全部内容为本发明所引用。如US 5703436及US 5707745所例示阴极的全部内容为本发明所引用,该阴极具有金属薄层,如:镁/银(Mg:Ag),及以溅射沉积覆盖金属薄层的透明导电层(ITO Layer)。US 6097147及US 20030230980所揭示各阻挡层的应用及原理,其全部内容为本发明所引用。US 20040174116所例示的注入层及同案所说明的保护层,其全部内容为本发明所引用。
未特别说明的结构及材料亦可应用于本发明,如US 5247190所揭示包括聚合物材料(PLEDs)的有机电致发光元件,其全部内容为本发明所引用。 再者,具有单一有机层的有机电致发光元件或如US 5707745所揭示堆栈形成的有机电致发光元件,其全部内容为本发明所引用。
除有特别限定,不同实施例中的任何层可使用任何适当方法来沉积形成。以有机层而言,较佳的方法包含如US 6013982及US 6087196所揭示的热蒸镀法及喷印法,其全部内容为本发明所引用;US 6337102所揭示有机气相沉积法(organic vapor phasedeposition,OVPD),其全部内容为本发明所引用;US 10/233470所揭示有机气相喷印沉积法(deposition by organic vapor jet printing,OVJP),其全部内容为本发明所引用。其他适当方法包含旋转涂布及以溶液为基础的制程。以溶液为基础的制程优选在氮气或惰性气体环境中进行。对于其他层而言,较佳的方法包含热蒸镀法。较佳的图案化方法包含如US6294398及US 6468819所揭示通过遮罩沉积再冷焊的制程,及整合喷印或有机气相喷印沉积与图案化的制程,其全部内容为本发明所引用。当然亦可使用其他方法。可调整用于沉积的材料以对应其所特用的沉积方法。
本发明式(I)所示化合物能以真空沉积或旋转涂布法制成应用于有机电致发光元件的非晶薄膜。当该化合物使用于任一上述有机层,其以高发光效率及低驱动电压展现出较长使用寿命及较佳热稳定性。
本发明的有机电致发光元件可应用于单一元件,其结构为阵列配置或阵列X-Y坐标中设有阴阳两极的元件。相较于习知元件,本发明能显著提升有机电致发光元件的发光效率及驱动稳定性。此外,与发光层中的磷光掺杂剂相结合,本发明的有机电致发光元件应用于全彩或多彩显示面板能实现较佳性能且可发射白光。
以下藉由实施例详细说明本发明的诸多性质及功效。该详述实施例仅用于说明本发明的性质,本发明不限于特定实施例所例示者。
合成例1(化合物1-4的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与3-(3-吡啶基)苯基硼酸(3-(3-Pyridyl)phenylboronic acid)(5.14g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去 离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物1-4(4.7g,产率40.5%)。
1H NMR(400MHz,CDCl3,δ):
9.943(s,1H);9.001-8.981(d,H);8.944(s,1H);8.776-8.763(d,1H);8.647-8.640(d,1H);8.436-8.391(t,4H);8.167(s,1H);7.982-7.961(d,1H);7.878-7.813(m,5H);7.741-7.633(m,5H);7.526-7.419(m,5H)。
合成例2(化合物1-5的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与3-二苯基硼酸(3-Biphenylboronic acid)(5.12g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物1-5(5.8g,产率50.0%)。
1H NMR(400MHz,CDCl3,δ):
9.946-9.943(d,1H);8.996-8.976(d,1H);8.777-8.760(d,1H);8.423-8.388(t,4H);8.161(s,1H);7.910-7.811(m,5H);7.718-7.632(m,6H);7.595-7.558(t,1H);7.526-7.476(m,5H);7.439-7.382(m,2H)。
合成例3(化合物1-6的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与二苯并呋喃-4-硼酸(dibenzofuran-4-boronic acid)(5.48g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的 去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物1-6(7.2g,产率60.6%)。
1H NMR(400MHz,CDCl3,δ):
9.965-9.961(s,1H);9.028-8.998(d,1H);8.784-8.768(d,1H);8.507-8.486(d,2H);8.424-8.403(d,2H);8.208(s,1H);8.177-8.155(d,2H);8.037-7.997(t,2H);7.842-7.821(d,2H);7.733-7.705(d,3H);7.658-7.637(d,1H);7.530-7.475(m,5H);7.439-7.377(m,2H)。
合成例4(化合物1-7的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与二苯并噻吩-4-硼酸(Dibenzothiophene-4-boronic acid)(5.89g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物1-7(7.1g,产率58.0%)。
1H NMR(400MHz,CDCl3,δ):
9.965-9.959(d,1H);9.015-8.996(m,1H);8.787-8.772(m,1H);8.469-8.407(m,4H);8.231-8.203(m,3H);7.995-7.974(d,2H);7.883-7.822(m,3H);7.726-7.703(d,2H);7.641-7.578(m,2H);7.531-7.403(m,6H)。
合成例5(化合物1-10的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-3-基-嘧啶 (4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基硼酸(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid(8.12g,258mmol))放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物1-10(3.1g,产率43.0%)。
1H NMR(400MHz,CDCl3,δ):
9.931(s,1H);8.992-8.969(d,1H);8.757(d,1H);8.369-8.362(d,4H);8.148(s,1H);7.929-7.910(d,1H);7.822-7.802(d,4H);7.729-7.644(m,7H);7.565-7.487(m,7H);7.433-7.386(m,4H)。
合成例6(化合物2-6的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-4-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-4-yl-pyrimidine)(10g,215mmol)与二苯并呋喃-4-硼酸(dibenzofuran-4-boronic acid)(5.48g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物2-6(9.6g,产率80.9%)。
1H NMR(400MHz,CDCl3,δ):
8.868-8.853(d,2H);8.617-8.602(d,2H);8.514-8.487(d,2H);8.424-8.403(d,2H);8.248(s,1H);8.187-8.160(d,2H);8.038-8.005(t,2H); 7.852-7.825(d,2H);7.734-7.703(m,3H);7.656-7.637(d,1H);7.534-7.478(m,4H);7.448-7.380(m,2H)。
合成例7(化合物2-10的合成)
将4-二苯基-4-基-6-(4-溴苯基)-2-吡啶-4-基-嘧啶(4-Biphenyl-4-yl-6-(4-bromophenyl)-2-pyridin-4-yl-pyrimidine)(10g,215mmol)与4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基硼酸(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid)(8.12g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物2-10(11g,产率78.0%)。
1H NMR(400MHz,CDCl3,δ):
δ8.847-8.833(d,2H);8.574-8.559(d,2H);8.390-8.359(m,4H);8.168(s,1H);7.932-7.912(d,1H);7.823-7.791(m,4H);7.730-7.687(t,4H);7.656-7.635(d,2H);7.586-7.486(m,5H);7.436-7.346(m,4H);7.314-7.258(t,2H)。
合成例8(化合物12-4的合成)
将4-二苯基-4-基-6-(3-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与(3-(3-吡啶基)苯基硼酸(3-(3-Pyridyl)phenylboronic acid)(5.14g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱, 蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物12-4(8.7g,产率75.0%)。
1H NMR(400MHz,CDCl3,δ):
9.933-9.937(s,1H);8.987-8.950(t,2H);8.766-8.755(d,1H);8.644-8.632(d,1H);8.531(s,1H);8.403-8.382(d,2H);8.314-8.294(d,1H);8.167(s,1H);7.987-7.966(d,1H);7.888(s,1H);7.847-7.638(m,9H);7.518-7.400(m,5H)。
合成例9(化合物12-6的合成)
将4-二苯基-4-基-6-(3-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与二苯并呋喃-4-硼酸(dibenzofuran-4-boronic acid)(5.48g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物12-6(8.1g,产率68.0%)。
1H NMR(400MHz,CDCl3,δ):
9.970(d,1H);9.022-8.992(d,1H);8.848-8.840(t,1H);8.770-8.761(d,1H);8.415-8.394(d,2H);8.362-8.342(d,1H);8.209(s,1H);8.139-8.121(d,1H);8.046-8.008(t,2H);7.824-7.641(m,4H);7.534-7.466(m,5H);7.431-7.378(m,2H)。
合成例10(化合物12-10的合成)
将4-二苯基-4-基-6-(3-溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3-bromophenyl)-2-pyridin-3-yl-pyrimidine)(10g,215mmol)与4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基硼酸(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenylboronic acid)(8.12g,258mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去 离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物12-10(7.8g,产率55.4%)。
1H NMR(400MHz,CDCl3,δ):
9.925(s,1H);8.977-8.959(d,1H);8.767-8.757(d,1H);8.490(s,1H);8.398-8.377(d,1H);8.272-8.251(d,1H);8.140(s,1H);7.931-7.911(d,1H);7.823-7.776(t,3H);7.748-7.631(m,8H);7.583-7.471(m,7H);7.433-7.346(m,4H)。
合成例11(化合物23-6的合成)
将4-二苯基-4-基-6-(3,5-二溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3,5-dibromo-phenyl)-2-pyridin-3-yl-pyrimidine(10g,184mmol))与二苯并呋喃-4-硼酸(dibenzofuran-4-boronic acid)(8.6g,406mmol)放入反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物23-6(7.2g,产率54.4%)。
1H NMR(400MHz,CDCl3,δ):
δ10.009-10.003(d,1H);9.053-9.033(d,1H);8.887-8.883(s,2H);8.778-8.766(d,1H);8.627(t,1H);8.440-8.418(d,2H);8.302(s,1H);8.064-8.045(d,1H);7.854-7.807(m,4H);7.707-7.651(m,4H);7.572-7.469(m,7H);7.423-7.387(m,3H)。
合成例12(化合物23-8的合成)
将4-二苯基-4-基-6-(3,5-二溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3,5-dibromo-phenyl)-2-pyridin-3-yl-pyrimidine(10g,184mmol))与萘-1-基硼酸(Naphthalen-1-ylboronic acid(7.9g,459mmol))放入 反应瓶中,再加入甲苯100毫升,再将K2CO3(4.46g,323mmol)溶解于40毫升的去离子水中加入反应瓶内,加入Pd(PPh3)4(0.371g,0.3mmol)再加入酒精20毫升,搅拌及于80℃回流反应16小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得白色固体的化合物23-8(11g,产率94.0%)。
1H NMR(400MHz,CDCl3,δ):
9.905(d,1H);8.928-8.923(d,1H);8.720(d,1H);8.503(s,2H);8.383-8.352(d,2H);8.192(s,1H);8.123-8.103(d,2H);7.977-7.941(t,4H);7.869(d,1H);7.790-7.759(d,2H);7.684-7.380(m,14H)。
合成例13(化合物36-1的合成)
将4-二苯基-4-基-6-(3,5-二溴苯基)-2-吡啶-3-基-嘧啶(4-Biphenyl-4-yl-6-(3,5-dibromo-phenyl)-2-pyridin-3-yl-pyrimidine(10g,184mmol))、咔唑carbazole(7.1g,424mmol)与STB(13.116g,136mmol)放入反应瓶中,再加入甲苯150毫升并搅拌,再加入Pd(dba)2(0.673g,1.17mmol)与P(t-butyl)3(0.662g,0.312mmol)并搅拌及于115℃回流反应18小时。反应完后加入150毫升去离子水搅拌至室温,过滤出固体并以去离子水跟丙酮清洗,该固体再加入200毫升去离子水、50毫升甲醇及50毫升丙酮的混合溶液中搅拌30分钟,再过滤,重复2次。烘干该固体,再以1000ml甲苯加热溶解后,通过硅胶柱,蒸馏浓缩后加入300ml甲醇搅拌30分钟过滤,烘干得黄色固体的化合物36-1(6.3g,产率48.0%)。
1H NMR(400MHz,CDCl3,δ):
9.898-9.894(d,1H);8.940-8.910(d,1H);8.752-8.736(d,1H);8.640-8.635(d,2H);8.380-8.354(d,2H);8.219-8.200(d,4H);8.163(s,1H);8.038-8.028(t,1H);7.799-7.768(d,2H);7.682-7.631(m,6H);7.519-7.345(m,12H)。
实施例1(有机电致发光元件的制造)
于基底载入蒸镀系统使用前,先以溶剂及紫外线臭氧清洗基底进行脱脂。之后,将基底传送至真空沉积室,于基底的顶部沉积所有层。由加热的 蒸镀舟(boat)在约10-6托的真空度依序沉积图2所示的各层:
a)空穴注入层,厚度20纳米,HAT-CN;
b)空穴传输层,厚度60纳米,HT;
c)发光层,厚度30纳米,包含掺杂有3%体积比BD的BH,(BH和BD为中国台湾昱镭光电科技股份有限公司的商品名);
d)电子传输层,厚度25纳米,包含化合物1-4及掺杂的喹啉锂(Liq);
e)电子注入层,厚度1纳米,氟化锂(LiF);及
f)阴极,厚度约150纳米,包含A1。
元件结构可表示如:ITO/HAT-CN(20纳米)/HT(60纳米)/BH-3%BD(30纳米)/化合物1-4:Liq(25纳米)/氟化锂(1纳米)/A1(150纳米)。
于沉积形成上述各层后,该元件自沉积室传送至干燥箱中,随即以UV可固化环氧树脂及含有吸湿剂的玻璃盖板进行封装。该有机电致发光元件具有3平方毫米的发光区域。于连接外部电源后,该有机电致发光元件于直流电压下运作,其所发光性质确认于后列表1。
所有制成的有机电致发光元件的电致发光性质均使用定电流源(KEITHLEY 2400Source Meter,made by Keithley Instruments,Inc.,Cleveland,Ohio)及光度计(PHOTORESEARCH SpectraScan PR 650,made by Photo Research,Inc.,Chatsworth,Calif.)于室温下进行测量。
藉由驱动定电流依据发光层的光色于室温及不同初始发光度来测试元件的使用寿命(或称稳定性)。光色使用国际照明委元会所定CIE坐标表示。
除将实施例1中电子传输层的化合物1-4各别置换为化合物1-6、1-7、12-6、23-8及36-1,实施例2、实施例3、实施例4、实施例5及实施例6如实施例1的层结构。
比较例1(有机电致发光元件的制造)
除将实施例1中电子传输层的化合物1-4置换为ET(中国台湾昱镭光电科技股份有限公司),比较例1的制造近似于实施例1的层结构。比较例1的元件结构可表示如:ITO/HAT-CN(20纳米)/HT(60纳米)/BH-3%BD(30纳米)/ET:Liq(20纳米)/LiF(1纳米)/A1(150纳米)。
制成的有机电致发光元件的发光的波峰波长、最大发光效率、驱动电压及稳定性列示于表1。图4为制成的有机电致发光元件的电致发光光谱。
表1
本发明不限于上述实施例、方法及实例,以请求保护本发明的范围及精神内所有实施例及方法为准。
实用性
如上所述,包含适用于有机电致发光元件材料的本发明的有机电致发光元件可实现长使用寿命的特性,并具有高发光效率和维持低的驱动电压。因此,本发明有机电致发光元件具有极高的技术价值且适用于平面显示器、行动通信元件的显示器、利用其为面发光体特性的光源、记号板。
Claims (14)
1.一种用于有机电致发光元件的式(I)化合物:
式中,
X1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
A1表示经取代或未经取代的(C6-C30)芳基、经取代或未经取代的(5至30元)杂芳基;
X1及A1为相同或相异;以及
n表示1或2的整数,当n表示2时,A1各自为相同或相异;且当X1为经取代或未经取代的(C6-C30)芳基时,n为1。
2.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,
X1表示经取代或未经取代的(C6-C20)芳基、经取代或未经取代的(5至20元)杂芳基,该(5至20元)杂芳基含有至少一个选自N、O及S所组成组中的杂原子;以及
A1表示经取代或未经取代的(C6-C20)芳基、经取代或未经取代的(5至20元)杂芳基,该(5至20元)杂芳基含有至少一个选自N、O及S所组成组中的杂原子。
3.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,该(C6-C30)芳基经选自(C1-C10)烷基、(C6-C30)芳基及(5至30元)杂芳基所组成组中的至少一种取代基取代,且该(5至30元)杂芳基经(C6-C30)芳基取代;以及
该(5至30元)杂芳基经选自(C1-C10)烷基、(C6-C30)芳基及(5至30元)杂芳基所组成组中的至少一种取代基取代,且该(5至30元)杂芳基经(C6-C30)芳基取代。
4.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,该(C6-C30)芳基经选自(C1-C5)烷基、(C6-C10)芳基及苯并咪唑基所组成组中的至少一种取代基取代,且该苯并咪唑基经(C6-C10)芳基取代;以及
该(5至30元)杂芳基经选自(C1-C5)烷基、(C6-C10)芳基及苯并咪唑基所组成组中的至少一种取代基取代,且该苯并咪唑基经(C6-C10)芳基取代。
5.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,A1表示式(II)或式(III)化合物:
式中,
Ar1及Ar2各自独立表示未经取代的(C6-C20)(亚)芳基,式(II)化合物藉由Ar1或Ar2与式(I)化合物连接,或式(II)化合物藉由Ar1及Ar2与式(I)化合物形成稠合环;
Z1表示N、O、S、CMe2或CH2,其中,当Z1为N时,式(III)化合物藉由Z1与式(I)化合物连接,且当Z1为O、S、CMe2或CH2时,式(III)化合物藉由其所具的苯基与式(I)化合物连接。
6.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,当n为1时,该式(I)化合物为式(I-1)或式(I-2)所示:
7.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,当n为2时,该式(I)化合物为式(I-3)所示:
8.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,X1选自下列所组成组中的一者:
9.如权利要求1所述的用于有机电致发光元件的式(I)化合物,其特征在于,A1选自下列所组成组中的一者:
10.一种有机电致发光元件,包含:
阴极;
阳极;以及
有机层,介于该阴极与阳极之间,且该有机层包含如权利要求1所述的式(I)化合物。
11.如权利要求10所述的有机电致发光元件,其特征在于,以该有机层的重量计算,式(I)化合物的含量为25%至100%,且该有机层的厚度为1纳米至500纳米。
12.如权利要求10所述的有机电致发光元件,其特征在于,该有机层是电子传输层,且该电子传输层包含式(I)化合物。
13.如权利要求12所述的有机电致发光元件,其特征在于,该电子传输层还包含n型导电掺杂剂,且该n型导电掺杂剂的含量为大于0wt%至75wt%。
14.如权利要求10所述的有机电致发光元件,其特征在于,该有机层是电子传输层、电子注入层、发光层、空穴阻挡层或电子阻挡层,且该发光层包含荧光或磷光发光体。
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